Dimercaptoisotrithione

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Structural formula
Structure of dimercaptoisotrithione
General
Surname Dimercaptoisotrithione
other names
  • DMIT
  • 1,3-dithiol-2-thione-4,5-dithiolate
Molecular formula C 3 S 5 2−
External identifiers / databases
CAS number
  • 62025-91-6 (thiol)
  • 54995-24-3 (sodium salt)
Wikidata Q1225721
properties
Molar mass 196.35 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dimercaptoisotrithione (abbreviation: DMIT ) is an ion that forms an intense red disodium salt . It is formed when excess carbon disulfide reacts with sodium in dimethylformamide as a solvent .

The molecule consists of a heterocycle that contains two sulfur atoms ( dithiol , see Hantzsch-Widman system ), a thione group S = C and two anionic thiolate (“mercapto”) groups.

Dimercaptoisotrithione was described by Steimecke in 1979 and, as an easily accessible dithiolate, belongs to the group of dithiol ("Dimercapto") ligands (note: this does not mean the heterocycle dithiol!).

It is isolated by reaction with zinc salts in the presence of tetraethyl or other tetraalkyl ammonium salts as (NR 4 ) 2 [Zn (DMIT) 2 ], which is sparingly soluble in water and stable to air with respect to oxygen . This serves as a storage form of Dimercaptoisotrithion and reacts similarly to the latter with nucleophiles to the corresponding Isotrithion - derivatives .

Dimercaptoisotrithione and (NR 4 ) 2 [Zn (DMIT) 2 ] can be converted into Tetrathia fulvalene and other sulfur-rich heterocycles.

The dimercaptoisotrithione ion, dissolved in dimethylformamide, is rearranged from 120 ° C into the more stable dimercaptotrithione ion (short name: DMT ; 1,3-dithiol-2-thione-4,5-dithiolate ).

literature

  • Niels Svenstrup, Jan Becher: The Organic Chemistry of 1,3-Dithiole-2-thione-4,5-dithiolate (DMIT). In: Synthesis. 1995, pp. 215-235, doi : 10.1055 / s-1995-3910 .

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.